Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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4:36 minutes

Problem 3

Textbook Question

What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl₃?

Verified step by step guidance

Identify the reactants: Methylmagnesium chloride (CH₃MgCl) is a Grignard reagent, and GaCl₃ is gallium trichloride, a Lewis acid.

Understand the reactivity: Grignard reagents are nucleophilic and can react with electrophilic centers, such as the gallium atom in GaCl₃, which has vacant orbitals.

Determine the stoichiometry: The problem specifies 'excess methylmagnesium chloride,' meaning multiple equivalents of CH₃MgCl will react with GaCl₃. Each CH₃ group can replace a Cl atom on GaCl₃.

Predict the product: The reaction will result in the substitution of all three Cl atoms in GaCl₃ with CH₃ groups from CH₃MgCl, forming Ga(CH₃)₃ (trimethylgallium) as the organometallic compound.

Verify the reaction mechanism: The reaction proceeds via nucleophilic attack of the CH₃ group on the gallium center, displacing Cl⁻ ions stepwise until all three Cl atoms are replaced by CH₃ groups.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Organometallic Compounds

Organometallic compounds are chemical species that contain a bond between a carbon atom of an organic molecule and a metal. These compounds are crucial in organic synthesis and catalysis, as they can act as nucleophiles or bases. Understanding their reactivity and how they interact with other compounds is essential for predicting the products of reactions involving organometallics.

Grignard Reagents

Grignard reagents are a class of organometallic compounds formed by the reaction of alkyl or aryl halides with magnesium metal. Methylmagnesium chloride (CH3MgCl) is a common example, and it acts as a strong nucleophile in reactions. When Grignard reagents react with electrophiles, they can form new carbon-carbon bonds, making them valuable in organic synthesis.

Lewis Acids and Bases

Lewis acids are substances that can accept an electron pair, while Lewis bases are those that can donate an electron pair. In the context of the reaction between methylmagnesium chloride and GaCl3, gallium trichloride acts as a Lewis acid. Understanding the roles of Lewis acids and bases is vital for predicting the outcome of reactions involving organometallic compounds and other electrophiles.

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Predict the product of the following aldehyde and ketone addition reactions.

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The situation shown here is an example where a cuprate is the only organometallic that will allow the product alcohol to be obtained. What is the problem with using a Grignard or an organolithium to attempt the same reaction?

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What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl3?

Key Concepts

Organometallic Compounds

Grignard Reagents

Lewis Acids and Bases

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What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl₃?